919802-97-4

Upstream product

• 191980-54-8 4-iodo-1-(triphenylmethyl)-1H-pyrazole 
• 95162-14-4 4-bromo-1-trityl-1H-pyrazole 
• 98-80-6 phenylboronic acid 
• 76-83-5 trityl chloride 

Downstream Products

• 10199-68-5 4-phenyl-1H-pyrazole 
• 1318759-77-1 2-diethylamino-3-methyl-5-phenylpyridine 
• 1318759-80-6 2-dibenzylamino-3-methyl-5-phenylpyridine 
• 10198-81-9 5-phenyl-2-(pyridin-2-yl)pyrimidine 
• 101161-83-5 3-phenyl-5,6,7,8-tetrahydroquinoline 
• 101161-85-7 6,7-dihydro-3-phenyl-5H-1-pyrindine 
• 106636-96-8 5-phenyl-1,2,3-triazine 
• 99939-04-5 4-Phenyl-1H-pyrazol-1-amin 
• 29134-16-5 2,5-diphenylpyrimidine 
• 136364-30-2 2-ethoxy-5-phenylpyridine 
• 34771-47-6 2-methyl-5-phenylpyrimidine 

Relevant academic research and scientific papers

Inverse electron demand diels-alder reactions of 1,2,3-triazines: Pronounced substituent effects on reactivity and cycloaddition scope

A systematic study of the inverse electron demand Diels-Alder reactions of 1,2,3-triazines is disclosed, including an examination of the impact of a C5 substituent. Such substituents were found to exhibit a remarkable impact on the cycloaddition reactivity of the 1,2,3-triazine without altering, and perhaps even enhancing, the intrinsic cycloaddition regioselectivity. The study revealed not only that the reactivity may be predictably modulated by a C5 substituent (R = CO2Me > Ph > H) but also that the impact is of a magnitude to convert 1,2,3-triazine (1) and its modest cycloaddition scope into a heterocyclic azadiene system with a reaction scope that portends extensive synthetic utility, expanding the range of participating dienophiles. Significantly, the studies define a now powerful additional heterocyclic azadiene, complementary to the isomeric 1,2,4-triazines and 1,3,5-triazines, capable of dependable participation in inverse electron demand Diels-Alder reactions, extending the number of complementary heterocyclic ring systems accessible with implementation of the methodology.

Synthesis of 4-aryl-1H-pyrazoles by Suzuki-Miyaura cross coupling reaction between 4-bromo-1H-1-trityl-pyrazole and arylboronic acids

A general procedure for the synthesis of 4-aryl-1H-pyrazoles by the Suzuki-Miyaura cross coupling reaction between 4-bromo-1H-1-tritylpyrazole and commercially available arylboronic acids was developed. Using this procedure, a direct synthesis of 4-aryl-1H-pyrazoles possessing functional groups, such as hydroxyl, nitro, and amino groups, on the aryl ring was realized. Those molecules could not be prepared by our previous synthesis of 4-aryl-1H-pyrazoles via the Kumada cross coupling reaction.

Synthesis of 4-arylpyrazoles via PdCl2(dppf)-catalyzed cross coupling reaction with Grignard reagents

4-Aryl-l-tritylpyrazoles were prepared from the cross coupling reaction of aryl Grignard reagents with 4-bromo-1-tritylpyrazoles in the presence of 0.2 mol% PdCl2(dppf) as catalyst. To deprotect the trityl group, 4-phenyl-l-tritylpyrazole was r